The first total synthesis of racemic 3-deoxy-7,8-dihydromorphine has been completed. The route utilized m-methoxyphenethylamine as starting material and employed Grewe cyclization of a hexahydroisoquinoline as the key step which formed the 4-hydroxymorphinan carbon-nitrogen skeleton. Oxide bridge closure of this intermediate followed by adjustment of the oxidation state then afforded racemic 3-deoxy-7,8-dihydromorphine. The monobromo product obtained by treatment of (-)-4-hydroxy-N-methylmorphinan-6-one with 1 mole of bromine in acetic acid has been determined to be the 1-bromo derivative by x-ray crystal analysis. A novel oxide bridge closure was developed during this work that affords 4,5-epoxymorphinan-6-ones from the 4-hydroxy precursors without aromatic bromination and with only 1 mole of bromine. Pharmacological evaluation of a number of compounds prepared in this work is reported under project number Z01 AM 19228-02 LC.